GB719282A - Improvements in the production of vat dyestuffs of the anthraquinone series - Google Patents

Improvements in the production of vat dyestuffs of the anthraquinone series

Info

Publication number
GB719282A
GB719282A GB23217/52A GB2321752A GB719282A GB 719282 A GB719282 A GB 719282A GB 23217/52 A GB23217/52 A GB 23217/52A GB 2321752 A GB2321752 A GB 2321752A GB 719282 A GB719282 A GB 719282A
Authority
GB
United Kingdom
Prior art keywords
chloride
acetylanthraquinone
carboxylic acid
amino
diamino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB23217/52A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB719282A publication Critical patent/GB719282A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16—Amino-anthraquinones
    • C09B1/20—Preparation from starting materials already containing the anthracene nucleus
    • C09B1/36—Dyes with acylated amino groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,5- and 1,8-Dinitro-2-ethylanthraquinones are obtained by nitration from 2-ethylanthraquinone and separation from each other by fractional precipitation.ALSO:The invention comprises 1-amino-2-acetyl-anthraquinone having attached to at least one of the other a -positions a monosubstituted amino group, the substituent of which is an acyl group derived from a carboxylic acid or a nitrogenous heterocyclic radical containing in one of the six-membered rings at least twice the group: <FORM:0719282/IV(c)/1> said heterocyclic radical being attached by a carbon atom of the heterocyclic ring to the nitrogen of the amino group. The invention also includes a process of heating 1-amino-2-acetylanthraquinones which contain an amino group in at least one further a -position and which may also contain other substituents in the anthraquinone nucleus with carboxylic acid halides or with compounds which contain at least once the above grouping in a six-membered heterocyclic ring. Preferably, the reactants are combined in equimolecular proportions, and when polyfunctional acylating agents are used, unreacted functional groups thereof may be reacted with other amines, such as aniline or 1-aminoanthraquinone. The products dye natural or regenerated cellulose or nylon red to black shades. In examples, 1.4-diamino-2-acetylanthraquinone is reacted in dichlorbenzene or nitrobenzene with (1) benzoyl chloride, or alkyl, alkoxy or halogen derivatives thereof, (2) diphenyl-4-carboxylic chloride, (3) pyridine-3- or 4-carboxylic chloride, (4) naphthalene-2-carboxylic chloride, (5) isophthaloyl or terephthaloyl chloride, (6) diphenyl-4.41-dicarboxylic chloride, (7) naphthalene-2.6-dicarboxylic acid chloride, (8) azobenzene-4.41-dicarboxylic acid chloride, (9) anthraquinone-2-carboxylic acid chloride or its 1-amino or 1-nitro derivatives, (10) 1-amino, nitro-, or acylamino anthraquinone-3-carboxylic acid chloride, (11) 1.9-thiazolanthrone-2-carboxylic acid chloride, (12) 1.9-anthrapyrimidine-2-carboxylic acid chloride, (13) 2.4-dichlor-6-methylpyrimidine, (14) 2.4-dichlor-6-phenylpyrimidine, (15) 2.4.6-trichlorquinazoline or 2.4-dichlorquinazoline, (16) 2.4-dichlor-6.7-benzquinazoline, (17) 2.4-dichlor-6.7-benzpteridine, (18) dichlorophthalazine, (19) cyanuryl chloride, (20) 2.4-dichloroquinazoline, together with 1 mol. 1-aminoanthraquinone, (21) 2-phenyl-4-chlor-6.7-phthaloylquinazoline. Also in examples, 1.5-diamino-2-acetylanthraquinone is similarly reacted with (22) fumaryl chloride, or chlorfumaryl chloride, (23) acetyl chloride, (24) propionyl chloride, (25) butyryl chloride, (26) iso- or terephthaloyl chloride, (27) 1-chlorisophthaloyl chloride, (28) diphenyl-3.31-dicarboxylic acid chloride, (29) 1-nitroanthraquinone-2-carboxylic acid chloride, (30) 3.4-phthaloylacridone-7-carboxylic acid chloride, (31) 2.4-dichlorquinazoline, (32) cyanuryl chloride, (33) 2-chlorquinoline-4-carboxylic acid chloride. Also in examples (34) 1.5-diamino-4-chlor-2-acetyl-anthraquinone is reacted with isophthaloyl chloride or 2.4-dichlorquinazoline; (35) 1.4.5-triamino-2-acetylanthraquinone is reacted with benzoyl chloride; (36) 1.5-diamino-8-hydroxy-2-acetylanthraquinone is reacted with isophthaloyl chloride; (37) 1.8-diamino-2-acetylanthraquinone is reacted with isophthaloyl chloride. Other acid halides specified are oxalyl chloride, stearic acid chloride, trimesic acid chloride, pyridine 3- and 4-carboxylic acid chlorides, quinoline-6-carboxylic acid chloride, and other compounds containing the grouping specified are 2.4-dichlor- or dibrom-pyrimidine, 2.5-dichlorpyrazine, 2.6-dichlor-4-methyl-1.3.5-triazene,2-(anthraquinonyl-2') -4-chlorquinazoline, 1.3-di (41-chlor-61, 71 phthaloylquinazoyl-21) benzene, 1.4-dichlorphthalazine, 4.41-dichlor-6.61-diphenyl-2.21-dipyrimidyl, cyanine bromide, trichlorpurine. 1.5- and 1.8-Diamino-2-acetylanthraquinone are obtained by consecutive treatment with oleum, ferrous sulphate and sodium sulphide from 1.5- and 1.8-dinitro-2-ethylantharaquinone. A hydroxy group may be introduced in 8-position by lengthening the oleum treatment. 1-amino-4-chlor-5-nitro-2-acetyl-anthraquinone is obtained by chlorination with sulphuryl chloride of 1-amino-5-nitro-2-acetyl -anthraquinone. 1.5 Diamino-4-chlor-2-acetylanthraquinone is obtained by reduction with sodium sulphide from 1-amino-4-chlor-5-nitro-2-acetylanthraquinone. 1.4.5-Triamino-2-acetylanthraquinone is prepared from 1-amino-5-nitro-4-chlor-2-acetylanthraquinone by reaction with p-toluene sulphonamide and saponification to 1.4-diamino-5-nitro-2-acetylanthraquinone which is then reduced with sodium sulphide.
GB23217/52A 1951-09-20 1952-09-16 Improvements in the production of vat dyestuffs of the anthraquinone series Expired GB719282A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE313561X 1951-09-20

Publications (1)

Publication Number Publication Date
GB719282A true GB719282A (en) 1954-12-01

Family

ID=6141160

Family Applications (1)

Application Number Title Priority Date Filing Date
GB23217/52A Expired GB719282A (en) 1951-09-20 1952-09-16 Improvements in the production of vat dyestuffs of the anthraquinone series

Country Status (4)

Country Link
US (1) US2731464A (en)
CH (1) CH313561A (en)
FR (1) FR1065696A (en)
GB (1) GB719282A (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE561166A (en) * 1956-09-27
US3126382A (en) * 1959-11-20 1964-03-24 O nhxocx
IT1000312B (en) * 1973-01-02 1976-03-30 Basf Ag PROCEDURE FOR THE DIRECT PREPARATION OF 1, 9 ANTRAPIRIMIDIN 2 CARBOSSI I ANTHRACHINONYLAMIDE IN THE FORM OF PIGMENTS

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH203953A (en) * 1937-07-29 1939-04-15 Chem Ind Basel Process for the production of an anthraquinone derivative.
US2567821A (en) * 1948-01-30 1951-09-11 Ciba Ltd Acylamino-anthraquinone vat dyestuffs

Also Published As

Publication number Publication date
FR1065696A (en) 1954-05-28
CH313561A (en) 1956-04-30
US2731464A (en) 1956-01-17

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